CN109942845A - A kind of preparation method of photoetching gum resin - Google Patents
A kind of preparation method of photoetching gum resin Download PDFInfo
- Publication number
- CN109942845A CN109942845A CN201910134364.1A CN201910134364A CN109942845A CN 109942845 A CN109942845 A CN 109942845A CN 201910134364 A CN201910134364 A CN 201910134364A CN 109942845 A CN109942845 A CN 109942845A
- Authority
- CN
- China
- Prior art keywords
- monomer
- ester
- solvent
- preparation
- added
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
Landscapes
- Polymerisation Methods In General (AREA)
Abstract
The invention discloses a kind of preparation methods of photoetching gum resin, comprising: the preparation of prepolymer: the monomer with acid activity group and the monomer with polar group being added in solvent, the quality of solvent is 1~4 times of monomer gross mass；After monomer dissolution, initiator is added, obtains prepolymer after dissolution；It is added solvent in the reaction vessel, quality is 1~4 times of monomer gross mass, stirs and is warming up to 60 DEG C~100 DEG C in a nitrogen atmosphere, and dropwise addition prepolymer drips in 2.5h~4h, rear constant temperature back flow reaction 15h~25h is added dropwise；The resinous polymer solution obtained after reaction is cooled to room temperature, using mixed precipitant precipitated resin solution, precipitating reagent dosage is 4~10 times of resinous polymer solution quality, after precipitation process, is filtered, is dried, obtains granular resin solid；The volume ratio of polar solvent and nonpolar solvent is 1 in mixed precipitant: (1~20).The present invention removes processing resinous polymer using the mixed precipitant of different proportion, can regulate and control to obtain different molecular weight；Also, the present invention can obtain smaller range of molecular weight distributions.
Description
Technical field
The present invention relates to a kind of preparations of fluoropolymer resin, and in particular to a kind of preparation side of the resin for photoresist
The control of the molecular weight of method more particularly to photoetching gum resin.
Background technique
Photoresist is the critical material of currently manufactured Advanced Integrated Circuits.Resin is particularly important in the composition of photoresist
One ingredient.Compared with the poly(4-hydroxystyrene) of KrF photoresist, (methyl) acrylic resin does not absorb at 193nm, energy
It is enough in the resin for preparing ArF photoresist, there is good high transparency and resolution ratio.But in order to reach the property of photoresist
It can require, need to control the molecular weight of methacrylic resin.For corresponding radical reaction, the main side of the control of molecular weight
Formula is to control inventory and reaction condition.Resin molecular weight that preferable polymerization reaction obtains is controlled usually to want meeting use
It is fluctuated in the range of asking.But this method can only realize the control of molecular weight to a certain extent, after not can solve runaway reaction
The improvement problem of resin molecular weight.
For methacrylic resin polymer, in the preparation usually using the lower alkanes of polarity as methyl
The precipitating reagent of acrylic polymer.If changing the composition of precipitating reagent, increases polar solvent wherein, keep content less
The resin of other molecular weight is dissolved, so that it may be separated by precipitating, optimize the distribution of resin molecular weight.The present invention is to upper
Imagination is stated to be studied.
Summary of the invention
Goal of the invention of the invention is to provide a kind of preparation method of photoetching gum resin, and realization improves methyl-prop after the reaction
The molecular weight of olefin(e) acid resinous polymer, to meet the needs of photoresist preparation.
To achieve the above object of the invention, the technical solution adopted by the present invention is that: a kind of preparation method of photoetching gum resin, packet
Include following steps:
(1) preparation of prepolymer: by one or more monomers with acid activity group and it is one or more have polar group
The monomer of group is added in solvent, and is made it completely dissolved, and wherein the quality of solvent is 1~4 times of monomer gross mass；To monomer
After dissolution, initiator is added, obtains prepolymer after dissolution；
(2) solvent is added in the reaction vessel, quality is 1~4 times of monomer gross mass, stirs and heats up in a nitrogen atmosphere
To 60 DEG C~100 DEG C, prepolymer is added dropwise, is dripped in 2.5h~4h, rear constant temperature back flow reaction 2h~25h is added dropwise；
(3) the resinous polymer solution obtained after reaction is cooled to room temperature, using mixed precipitant precipitated resin solution, is sunk
Agent dosage in shallow lake is 4~10 times of resinous polymer solution quality, after precipitation process, is filtered, is dried, obtains granular resin
Solid；Wherein, the mixed precipitant is mixed by polar solvent and nonpolar solvent, polar solvent and nonpolar solvent
Volume ratio is 1: (1~20).
In above-mentioned technical proposal, the amount of the substance total by monomer is in terms of 100%, and the dosage of monomer is respectively as follows:
Acid activity monomer: 30~70%,
Polar monomer: 70~30%.
Acid activity monomer in the photoetching gum resin containing different substituents may be acid activity (methyl) acrylate,
Its structure is to meet at least one of chemical general formula monomer, and specific acid activity monomer structure general formula is as follows:
R1=H, carbon atom number 1-20 carbon-containing group.
R2=acid-labile group.
Specifically, R2It is a kind of level Four ester of carbon atom number between 6-30, the carbon atom being connected with ester bond oxygen atom
Hydrogen atom all replaced by other groups, possible structure be tertiary butyl ester, substituted tert-butyl ester, alkyl-substituted Buddha's warrior attendant
Alkyl ester, alkyl-substituted adamantane derivative ester, alkyl-substituted norbornyl ester, alkyl-substituted norborneol derivative ester, alkane
Cyclic alkyl ester, alkyl-substituted cyclic alkyl derivative ester that base replaces etc. are one such or a variety of.
It may be (methyl) acrylic acid of polar functionalities containing one or more polar monomers in the photoetching gum resin
Ester, structure are to meet at least one of chemical general formula monomer, and specific polar monomer general structure is as follows:
R3The carbon-containing group of=H or carbon atom number in 1-20.
R4=polar group.
Specifically, R4For carbon atom number between 6 ~ 30 the ring-type, caged of hydroxyl or straight chain type containing carbon structure and all kinds of
Lactone structure, possible structure are the Buddha's warrior attendant alkyl ester containing one or more independent hydroxyls, the ring containing one or more independent hydroxyls
Own ester, the ring pentyl ester containing one or more independent hydroxyls, the polycyclic ester type compound containing one or more independent hydroxyls, containing 1 or
The caged ester type compound of multiple independent hydroxyls, valerolactone, replaces valerolactone, caprolactone, replaces caprolactone, containing gold butyrolactone
Lactone, the lactone containing multiring structure, the lactone containing cage structure of rigid alkyl structure etc. are one such or a variety of.
Preferred monomer dosage is, in mol:
1- cyclohexyl methyl acrylate: 4-10 parts；
Methacrylate butyrolactone: 3-9 parts；
3- hydroxyl -1- adamantyl methacrylate: 3-9 parts.
In above-mentioned technical proposal, preferred initiator is azodiisobutyronitrile, and quality is the 4%- of the amount of monomer total material
10%。
In above-mentioned technical proposal, preferred solvent is ethyl acetate, and precipitating reagent is dehydrated alcohol/n-hexane, volume ratio 1
: (1~20)
Preferred technical solution, in step (1), after monomer is added, logical nitrogen and carrying out ultrasonic agitation is dissolved completely in monomer
In solvent.
Preferred technical solution, in step (1), after initiator is added, oscillation dissolves initiator.
In the present invention, pass through the molecular weight of the proportion adjustment resin product of dehydrated alcohol and n-hexane.
Due to the above technical solutions, the present invention has the following advantages over the prior art:
The present invention removes processing methacrylic resin polymer using the dehydrated alcohol and n-hexane mixed precipitant of different proportion,
It can regulate and control to obtain different molecular weight；Also, the present invention can obtain smaller range of molecular weight distributions.
Specific embodiment
The present invention will be further described below with reference to examples:
A kind of embodiment: preparation method of photoetching gum resin, comprising the following steps:
(1) preparation of prepolymer: by the 1- cyclohexyl methyl acrylate of 24g, 10g methacrylic acid butyrolactone,
3- hydroxyl -1- the adamantyl methacrylate of 16g is placed in the single-necked flask containing ethyl, wherein for dissolving list
The ethyl acetate dosage of body is 130g, and the mixture in single-necked flask is led to nitrogen ultrasound to dissolution.After monomer dissolution, it is added
A certain amount of azodiisobutyronitrile accounts for the 4.9% of monomer gross mass as initiator, initiator amount 2g, content, shakes molten
Solution, for use.
(2) preparation of methacrylic resin polymer: in the four-hole boiling flask equipped with magnetic agitation, reflux condensing tube
A certain amount of ethyl acetate solution is added, dosage 50g is 1.11 times of monomer gross mass.Setting mixing speed is 400rpm,
Lead to nitrogen temperature to 80 DEG C of predetermined temperature, prepolymer is added dropwise, 3h is dripped, and rear constant temperature back flow reaction is added dropwise to 20h.
(3) intermediate processing handles methacrylic resin solution: by the methacrylic resin polymer solution after reaction
After cooling, using the dehydrated alcohol and n-hexane mixed precipitant precipitated resin solution of different proportion, wherein precipitating reagent dosage is
6 times of methacrylic resin polymer solution quality after precipitation process, are filtered, dry, obtain granular metering system
Acid resin.
On the basis of above-mentioned overall plan, the dehydrated alcohol of different proportion is set forth in following embodiment and comparative example
With n-hexane mixed precipitant treated situation.
Comparative example:
Pure hexane precipitation agent processing:
After the methacrylic resin polymer solution cooling after reaction, according to the n-hexane of 6 times of mass ratioes as precipitating reagent
Precipitating methacrylic resin polymer solution is removed, control mixing speed is 400rpm, and rate of addition 10mL/min is dripped
After stand half an hour, filter, it is dry, obtain granular methacrylic resin.Molecular weight is 5072, and molecular weight distribution is
1.980。
Embodiment one:
N-hexane: dehydrated alcohol=1, mixed precipitant processing:
Prepare n-hexane: the mixed precipitant of dehydrated alcohol=1.Methacrylic resin polymer solution after reaction is cooling
Afterwards, precipitating methacrylic resin polymer solution is removed according to the mixed precipitant of 6 times of mass ratioes, control mixing speed is
400rpm, rate of addition 10mL/min stand half an hour after dripping, filter, dry, obtain granular methacrylic acid
Resin.Molecular weight is 8969, molecular weight distribution 1.390.
Embodiment two:
N-hexane: dehydrated alcohol=2, mixed precipitant processing:
Prepare n-hexane: the mixed precipitant of dehydrated alcohol=2.Methacrylic resin polymer solution after reaction is cooling
Afterwards, precipitating methacrylic resin polymer solution is removed according to the mixed precipitant of 6 times of mass ratioes, control mixing speed is
400rpm, rate of addition 10mL/min stand half an hour after dripping, filter, dry, obtain granular methacrylic acid
Resin.Molecular weight is 7439, molecular weight distribution 1.468.
Embodiment three:
N-hexane: dehydrated alcohol=3, mixed precipitant processing:
Prepare n-hexane: the mixed precipitant of dehydrated alcohol=3.Methacrylic resin polymer solution after reaction is cooling
Afterwards, precipitating methacrylic resin polymer solution is removed according to the mixed precipitant of 6 times of mass ratioes, control mixing speed is
400rpm, rate of addition 10mL/min stand half an hour after dripping, filter, dry, obtain granular methacrylic acid
Resin.Molecular weight is 6824, molecular weight distribution 1.506.
Example IV:
N-hexane: dehydrated alcohol=4, mixed precipitant processing:
Prepare n-hexane: the mixed precipitant of dehydrated alcohol=4.Methacrylic resin polymer solution after reaction is cooling
Afterwards, precipitating methacrylic resin polymer solution is removed according to the mixed precipitant of 6 times of mass ratioes, control mixing speed is
400rpm, rate of addition 10mL/min stand half an hour after dripping, filter, dry, obtain granular methacrylic acid
Resin.Molecular weight is 6323, molecular weight distribution 1.574.
Conclusion:
From the point of view of the result of the above embodiments, compare the methacrylic resin polymer of pure hexane processing as a result, not
Dehydrated alcohol and n-hexane mixed precipitant in proportion can reach the molecular weight of control methacrylic resin polymer really
Purpose, and at the same time molecular weight distribution numerical value can be reduced.
It is provided only in the embodiment of the present invention using (methyl) acrylate as the resins synthesis of monomer, but the present invention can also answer
For other resins prepared in a manner of free radical polymerization, such as polystyrene resin.
Claims (10)
1. a kind of preparation method of photoetching gum resin, which comprises the following steps:
(1) preparation of prepolymer: by one or more monomers with acid activity group and it is one or more have polar group
The monomer of group is added in solvent, and is made it completely dissolved, and wherein the quality of solvent is 1~4 times of monomer gross mass；To monomer
After dissolution, initiator is added, obtains prepolymer after dissolution；
(2) solvent is added in the reaction vessel, quality is 1~4 times of monomer gross mass, stirs and heats up in a nitrogen atmosphere
To 60 DEG C~100 DEG C, prepolymer is added dropwise, is dripped in 2.5h~4h, rear constant temperature back flow reaction 2h~25h is added dropwise；
(3) the resinous polymer solution obtained after reaction is cooled to room temperature, using mixed precipitant precipitated resin solution, is sunk
Agent dosage in shallow lake is 4~10 times of resinous polymer solution quality, after precipitation process, is filtered, is dried, obtains granular resin
Solid；Wherein, the mixed precipitant is mixed by polar solvent and nonpolar solvent, polar solvent and nonpolar solvent
Volume ratio is 1: (1~20).
2. the preparation method of photoetching gum resin according to claim 1, it is characterised in that: the amount with the total substance of monomer is
100% meter, the dosage of monomer are respectively as follows:
Acid activity monomer: 30~70%,
Polar monomer: 70~30%.
3. the preparation method of photoetching gum resin according to claim 2, it is characterised in that: the acid activity monomer is containing acid
(methyl) acrylate of quick group, general structure are as follows:
In formula, R1It is H or carbon atom number in the carbon-containing group of 1-20, R2 is the functional group containing acid-labile group；
The polar monomer is (methyl) acrylate of polar functionalities, general structure are as follows:
In formula, R3Carbon-containing group for H or carbon atom number in 1-20, R4For the functional group of polar functionalities.
4. the preparation method of photoetching gum resin according to claim 3, it is characterised in that: R2The carbon atom number contained is in 6-
Between 30, the hydrogen atom for the carbon atom being connected with ester bond oxygen atom is all replaced by other groups, constitutes tertiary butyl ester, replaces
Tertiary butyl ester, alkyl-substituted Buddha's warrior attendant alkyl ester, alkyl-substituted adamantane derivative ester, alkyl-substituted norbornyl ester, alkyl
One of substituted norborneol derivative ester, alkyl-substituted cyclic alkyl ester, alkyl-substituted cyclic alkyl derivative ester
Or it is a variety of；
R4The carbon atom number contained is connected with ester bond oxygen atom between 6 ~ 30 and constitutes the Buddha's warrior attendant containing one or more independent hydroxyls
Alkyl ester, the ring pentyl ester containing one or more independent hydroxyls, contains one or more independences at the cyclohexyl containing one or more independent hydroxyls
The polycyclic ester type compound of hydroxyl, butyrolactone, valerolactone, replaces penta at the caged ester type compound containing one or more independent hydroxyls
Lactone, caprolactone, replace caprolactone, the lactone containing adamantane structure, the lactone containing multiring structure, in the lactone containing cage structure
It is one or more.
5. the preparation method of photoetching gum resin according to claim 1, it is characterised in that: the initiator is organic peroxy
Compound or azo-initiator, initiator quality are the 4%~10% of monomer gross mass；The initiator be cyclohexanone peroxide,
One of dibenzoyl peroxide, tert-butyl hydroperoxide, azodiisobutyronitrile, azobisisoheptonitrile are a variety of.
6. the preparation method of photoetching gum resin according to claim 1, it is characterised in that: the solvent is selected from acetic acid second
Ester, butyl acetate, acetic acid peopentyl ester, ethyl lactate, propylene glycol methyl ether acetate, propylene glycol list Acetic Ester, dihydroxypropane single-ether,
Tirethylene glycol methyl ether, tirethylene glycol ether, tetrahydrofuran, methyltetrahydrofuran, methanol, ethyl alcohol, the tert-butyl alcohol, isopropanol,
One of acetone, cyclohexanone, methyl ethyl ketone, methyl iso-butyl ketone (MIBK), toluene, dimethylbenzene, paraxylene or biphenyl are a variety of.
7. the preparation method of photoetching gum resin according to claim 1, it is characterised in that: by adjusting polar solvent and non-
The ratio of polar solvent adjusts the molecular weight of resin product.
8. the preparation method of photoetching gum resin according to claim 7, it is characterised in that: the polar solvent is selected from first
Alcohol, ethyl alcohol, the tert-butyl alcohol, isopropanol；The nonpolar solvent is selected from pentane, n-hexane, hexamethylene, heptane.
9. the preparation method of photoetching gum resin according to claim 1, it is characterised in that: in step (1), monomer is added
Afterwards, lead to nitrogen and carrying out ultrasonic agitation is completely dissolved monomer in a solvent.
10. the preparation method of photoetching gum resin according to claim 1, it is characterised in that: in step (1), be added and cause
After agent, oscillation dissolves initiator.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910134364.1A CN109942845A (en) | 2019-02-22 | 2019-02-22 | A kind of preparation method of photoetching gum resin |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910134364.1A CN109942845A (en) | 2019-02-22 | 2019-02-22 | A kind of preparation method of photoetching gum resin |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN109942845A true CN109942845A (en) | 2019-06-28 |
Family
ID=67007659
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910134364.1A Pending CN109942845A (en) | 2019-02-22 | 2019-02-22 | A kind of preparation method of photoetching gum resin |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN109942845A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111018758A (en) * | 2019-12-31 | 2020-04-17 | 山东益丰生化环保股份有限公司 | Sulfur-containing monomer, preparation method and application thereof |
| CN111718439A (en) * | 2020-06-19 | 2020-09-29 | 宁波南大光电材料有限公司 | Methacrylic resin and preparation method and application thereof |
| CN112679631A (en) * | 2020-12-22 | 2021-04-20 | 宁波南大光电材料有限公司 | Method for removing small molecular substances in synthetic resin |
| CN112759697A (en) * | 2020-12-29 | 2021-05-07 | 宁波南大光电材料有限公司 | Methacrylic resin and preparation method thereof |
| CN112920314A (en) * | 2021-01-26 | 2021-06-08 | 宁波南大光电材料有限公司 | Acid-activated resin and photoresist |
| CN113198549A (en) * | 2021-04-26 | 2021-08-03 | 宁波南大光电材料有限公司 | Method for removing metal impurities in photoresist resin |
| CN115260348A (en) * | 2022-09-30 | 2022-11-01 | 北京八亿时空液晶科技股份有限公司 | High molecular weight and narrow distribution PHS resin and preparation method and application thereof |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003122010A (en) * | 2001-10-16 | 2003-04-25 | Fuji Photo Film Co Ltd | Positive resist composition |
| WO2005006078A1 (en) * | 2003-07-09 | 2005-01-20 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, multilayer body, and method for forming resist pattern |
| CN1714110A (en) * | 2002-11-05 | 2005-12-28 | Jsr株式会社 | Acrylic copolymer and radiation-sensitive resin composition |
| CN101638374A (en) * | 2008-07-28 | 2010-02-03 | 住友化学株式会社 | Oxime compound and resist composition containing the same |
| CN103172787A (en) * | 2011-12-21 | 2013-06-26 | 德莎欧洲公司 | Adhesive masses with high mole masses and a dense mole mass distribution and process for their preparation |
| CN108373520A (en) * | 2017-12-22 | 2018-08-07 | 江苏汉拓光学材料有限公司 | A kind of acrylate copolymer and the photoetching compositions comprising it |
| CN108628101A (en) * | 2018-04-26 | 2018-10-09 | 儒芯微电子材料（上海）有限公司 | Electron beam lithography glue composition and preparation method |
-
2019
- 2019-02-22 CN CN201910134364.1A patent/CN109942845A/en active Pending
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2003122010A (en) * | 2001-10-16 | 2003-04-25 | Fuji Photo Film Co Ltd | Positive resist composition |
| CN1714110A (en) * | 2002-11-05 | 2005-12-28 | Jsr株式会社 | Acrylic copolymer and radiation-sensitive resin composition |
| WO2005006078A1 (en) * | 2003-07-09 | 2005-01-20 | Tokyo Ohka Kogyo Co., Ltd. | Resist composition, multilayer body, and method for forming resist pattern |
| CN101638374A (en) * | 2008-07-28 | 2010-02-03 | 住友化学株式会社 | Oxime compound and resist composition containing the same |
| CN103172787A (en) * | 2011-12-21 | 2013-06-26 | 德莎欧洲公司 | Adhesive masses with high mole masses and a dense mole mass distribution and process for their preparation |
| CN108373520A (en) * | 2017-12-22 | 2018-08-07 | 江苏汉拓光学材料有限公司 | A kind of acrylate copolymer and the photoetching compositions comprising it |
| CN108628101A (en) * | 2018-04-26 | 2018-10-09 | 儒芯微电子材料（上海）有限公司 | Electron beam lithography glue composition and preparation method |
Non-Patent Citations (1)
| Title |
|---|
| 郝立新等: "《高分子化学与物理教程》", 31 December 1997, 化学工业出版社 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111018758A (en) * | 2019-12-31 | 2020-04-17 | 山东益丰生化环保股份有限公司 | Sulfur-containing monomer, preparation method and application thereof |
| CN111018758B (en) * | 2019-12-31 | 2021-02-23 | 山东益丰生化环保股份有限公司 | Sulfur-containing monomer, preparation method and application thereof |
| CN111718439A (en) * | 2020-06-19 | 2020-09-29 | 宁波南大光电材料有限公司 | Methacrylic resin and preparation method and application thereof |
| CN112679631A (en) * | 2020-12-22 | 2021-04-20 | 宁波南大光电材料有限公司 | Method for removing small molecular substances in synthetic resin |
| CN112679631B (en) * | 2020-12-22 | 2022-07-08 | 宁波南大光电材料有限公司 | Method for removing small molecular substances in synthetic resin |
| CN112759697A (en) * | 2020-12-29 | 2021-05-07 | 宁波南大光电材料有限公司 | Methacrylic resin and preparation method thereof |
| CN112920314A (en) * | 2021-01-26 | 2021-06-08 | 宁波南大光电材料有限公司 | Acid-activated resin and photoresist |
| CN113198549A (en) * | 2021-04-26 | 2021-08-03 | 宁波南大光电材料有限公司 | Method for removing metal impurities in photoresist resin |
| CN115260348A (en) * | 2022-09-30 | 2022-11-01 | 北京八亿时空液晶科技股份有限公司 | High molecular weight and narrow distribution PHS resin and preparation method and application thereof |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN109942845A (en) | A kind of preparation method of photoetching gum resin | |
| JP5631550B2 (en) | Method for producing copolymer for photoresist | |
| CN1976913B (en) | Lactone compounds, lactone-containing monomers, their polymers, resist compositions using same, and processes for forming patterns using same | |
| TW201100448A (en) | Process for producing photoresist polymeric compounds | |
| US9546133B2 (en) | Method for producing copolymer for semiconductor lithography containing reduced amount of metal impurities, and method for purifying polymerization initiator for production of copolymer | |
| CN103588926B (en) | A kind of acrylic resin of cationic photocurable and preparation method thereof | |
| TW200424769A (en) | Process for refining crude resin for resist | |
| CN103261144A (en) | Acetoacetate-functional monomers and their uses in coating compositions | |
| CN107814868A (en) | Novel aqueous acrylic resin/polyurethane compound leather finishing agent prepared by a kind of Pickering emulsion polymerizations | |
| CN109369839A (en) | A kind of self-cross linking type vinyl chloride copolymer lotion and preparation method thereof | |
| CN101580565A (en) | Method for copolymerization of alpha-methyl styrene (AMS) and maleic anhydride (MAn) | |
| KR20100048896A (en) | Method for producing a copolymer solution with a uniform concentration for semiconductor lithography | |
| JPS6178808A (en) | Manufacture of insoluble and low swellability powdery polymer | |
| CN109942741A (en) | A kind of preparation method of photoresist resin | |
| CN100503686C (en) | Amphiphilic macrocyclic polymer and preparation method | |
| US7312294B2 (en) | Norbornane lactone (meth)acrylate and polymer thereof | |
| CN109880149A (en) | Preparation method of large-size polyurea hollow microspheres | |
| CN103965384B (en) | The preparation method of polymethylmethacrylate | |
| CN101348596A (en) | Emulsion containing greasy cyclopentenyl (methyl) acrylic ester monomer composition | |
| CN104292378A (en) | Nonspherical particle preparation method based on change of hydrophilicities and crosslinking degrees of seeds | |
| CN108047833A (en) | A kind of barrier glue without primer and preparation method thereof | |
| CN113980536B (en) | Formaldehyde absorption emulsion and preparation method and application thereof | |
| JP2014109022A (en) | Purification method of resin for photolithography | |
| JP2009235186A (en) | Production method of polymer for photoresist and distillation can used for the same | |
| CN106632805B (en) | A kind of preparation method of high conglutination-resistance acrylic emulsion |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| TA01 | Transfer of patent application right | ||
| TA01 | Transfer of patent application right |
Effective date of registration: 20201217 Address after: 315800 21 Qingshan Road, Chaiqiao street, Beilun District, Ningbo City, Zhejiang Province Applicant after: NINGBO NANDA OPTOELECTRONIC MATERIAL Co.,Ltd. Address before: 7 / F, Yueliangwan International Center, 9 Cuiwei street, Suzhou Industrial Park, Suzhou, Jiangsu Province Applicant before: JIANGSU NATA OPTO-ELECTRONIC MATERIAL Co.,Ltd. |
|
| RJ01 | Rejection of invention patent application after publication | ||
| RJ01 | Rejection of invention patent application after publication |
Application publication date: 20190628 |